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$1,000,000
3 Beds 4 Baths 220228495 MLS
Live the best of Ashland in this iconic re-built Victorian, blending timeless charm with tasteful modern updates. Just steps from restaurants, cafés, Cabaret Theatre, and a couple blocks from OSF, it feels private while offering true downtown living. Stone-surround wood-burning fireplace with redwood mantel and beautiful fir floors welcome you in. Formal dining and covered screened patio feature mountain views. Kitchen boasts Neolith quartz counters, copper farmhouse sink, induction cooktop, smart refrigerator, double ovens, skylight, and breakfast peninsula. 2 primary suites--one on each level--offer tiled baths, glass-enclosed showers, quartz vanities, and soaking tub upstairs. Terraced low-maintenance landscaping, automated irrigation, private patios, ample off-street parking, and a backup generator add convenience. Ally access to detached 2-car garage and studio apartment above with full kitchen, bath, and large balcony--perfect for guests, rental income, or flexible living.

364 Hargadine Street, Ashland

$3,700,000
4 Beds 1 Baths 220228293 MLS
Rare opportunity to own 127 acres in Eagle Point with approximately 80 irrigated acres from Little Butte Creek. This versatile property features an established vineyard with 10 varietals, an extensively remodeled farmhouse, brand-new office with modern accommodations including a restroom and kitchen, two wells, and a fully equipped winery. The winery retains the equipment used during years of wine production from 2005-2019, making this an ideal opportunity for someone looking to pursue or revive a vineyard and wine operation. The irrigated pasture has been carefully maintained and is fully set up for irrigation, making it ideal for cattle, hay production, or other agricultural uses. Solar panels provide approximately $20,000 in annual income, increasing toward $25,000. Combining irrigated acreage, vineyard, winery, remodeled improvements, water resources & solar income, 1098 Nick Young Rd offers a rare opportunity to create a distinctive Southern Oregon agricultural estate

1098 Nick Young Road, Eagle Point

$3,700,000
4 Beds 1 Baths 220228292 MLS
Rare opportunity to own 127 acres in Eagle Point with approximately 80 irrigated acres from Little Butte Creek. This versatile property features an established vineyard with 10 varietals, an extensively remodeled farmhouse, brand-new office with modern accommodations including a restroom and kitchen, two wells, and a fully equipped winery. The winery retains the equipment used during years of wine production from 2005-2019, making this an ideal opportunity for someone looking to pursue or revive a vineyard and wine operation. The irrigated pasture has been carefully maintained and is fully set up for irrigation, making it ideal for cattle, hay production, or other agricultural uses. Solar panels provide approximately $20,000 in annual income, increasing toward $25,000. Combining irrigated acreage, vineyard, winery, remodeled improvements, water resources & solar income, 1098 Nick Young Rd offers a rare opportunity to create a distinctive Southern Oregon agricultural estate

1098 Nick Young Road, Eagle Point

$978,000
6 Beds 5 Baths 220227457 MLS
LOCATION....LOCATION...LOCATION!! Brand new roofs have recently been installed on both properties and the historic Reames House is now Move in Ready! This one of a kind property is an incredibly rare find and just a short walk to downtown Jacksonville. This quaint little town is home to incredible restaurants, unique boutiques and the iconic Britt Music and Arts festival. Once a popular bed and breakfast, this property is rich with history and has been beautifully restored to accomodate a large two family set-up or can continue as a thriving BNB. A standout feature of this property is the separate tax lot that hosts the versatile Carriage House. A charming space that offers endless possibilities. In the past it too was enjoyed as a BNB. Today, it can easily be converted into a guest suite, art studio, or home office. Surrounded by lush gardens, a variety of fruit trees, and a peaceful patio. Don't miss out on this amazing opportunity to own a piece of Jacksonville History!

540 E California Street, Jacksonville

$450,000
4 Beds 3 Baths 220226637 MLS
This turn of the century house is conveniently located in down town Medford near the court house area right across from the catholic church. There are many possible investment opportunities for this property or use it as a residential. There are 5 rooms occupied out of 6 rooms that have been established and 4 full bathrooms and only one bathroom is shared. There are two room ensuites upstairs and one room ensuite down stairs with French doors. This could be a nice office area. Enter into a nice living room featuring a large wood fireplace. At the entrance is a walk-in closet space or another small office with a front window. Original hardwood floors, a separate large dining area with built in cupboards and drawers. kitchen has a large walk-in food pantry, four refrigerators, dishwasher and an island. The mornings are perfect to sit out on the front covered porch which has a ceiling fan to enjoy the sunrise. At the back of the house there are 4 sheds, a small covered deck.

Medford

$1,450,000
10 Beds 12 Baths 220225786 MLS
One block from the Oregon Shakespeare Festival and downtown Ashland's restaurants, galleries, and cultural amenities, the McCall House B&B is a beautifully restored 1883 Italianate home offered for sale as a private residence. Currently operating as a boutique hotel, the property features ten historic guest rooms, including two detached private Carriage House suites, and may continue as a licensed hospitality business for a buyer who wishes to carry on that tradition. The C-1 zoning also opens the door to a variety of commercial uses, including a restaurant, office suites, or other business opportunities. Ten on-site parking spaces are included, a welcome convenience this close to the Ashland Plaza. This is a rare opportunity to own one of the city's most celebrated historic addresses. Due to the C-1 zoning, conventional 30-year financing is unavailable, and non-cash buyers are encouraged to confirm lending options before requesting an appointment. Please do not disturb guests.

153 Oak Street, Ashland

$564,900
3 Beds 2 Baths 220225550 MLS
'One Property. Four Possibilities. Less than a mile from downtown Ashland, this classic Victorian offers exceptional flexibility with versatile zoning and mountain views. Enjoy it as a spacious 3-bedroom, 2-bath home, a duplex with two long-term rental units, a residence with a currently licensed short-term rental, or a live/work property with a private entrance ideal for an attorney, counselor, massage therapist, or other home-based business. Features include a spacious upstairs primary suite with full bath, basement storage, dry sauna, washer, dryer, refrigerator, an inviting patio, and three deeded off-street parking spaces. Historic charm meets modern opportunity in this truly one-of-a-kind Ashland property.'

508 N Main Street, Ashland

$996,000
5 Beds 3 Baths 220225227 MLS
Beautifully restored 1908 classic home located on a rare R2 zoned double lot just blocks from downtown Ashland's theatres, restaurants, galleries, and parks. MAIN RESIDENCE Featuring 3 bedrooms and 2 full baths, interior highlights include original fir floors, high ceilings, designer lighting, updated kitchen, pantry and abundant natural light throughout. Flexible layout supports guest space, office, or extended living arrangements. LOWER LEVEL Remodeled with separate entrance, kitchen, bedroom and full bathroom offering independent living space. Foundation of main home was updated in 1997 with central heat, air, electrical and plumbing systems. DETACHED COTTAGE Separate remodeled cottage with bedroom and bath ideal for additional flexible living needs, guest suite, or office. OUTDOOR FEATURES Mature landscaping with fenced yard, irrigation, water feature, dry sauna, spa, storage shed, and ample off street parking. ADDITIONAL HIGHLIGHTS R2 zoning ideal for income producing living.

541 Fairview Street, Ashland

$1,695,000
4 Beds 5 Baths 220225149 MLS
VIEWS, VIEWS, VIEWS! This exceptional property with breathtaking panoramic views sweeping from Eagle Point to Ashland offers Victorian charm paired with modern comfort. Just under 5 Acres and almost 4300 sq ft, this 4 bedroom 5 bath residence, features two complete living quarters, each with its own full kitchen, private entrance, and laundry area, making it ideal for multigenerational living, family, guests, or rental income potential. The upper level is enhanced by balconies on each side of the home providing the perfect place to enjoy morning coffee and evening nights. Also featuring a Stiltz Elevator for convenient access to upper level. Main level of the home has a great floor plan with space for everyone inside and out with a covered porch. The four-car garage provides abundant space for vehicles, toys and storage. Ideally located just minutes from the historic town of Jacksonville, wineries, and shopping, this home is truly incredible.

4303 Tami Lane, Central Point

$759,000
5 Beds 6 Baths 220221349 MLS
71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, Ashland

$549,000
5 Beds 2 Baths 220213933 MLS
$10,000. CREDIT TO BUYER for closing cost or points buy down. Built in1890 the second- oldest home in East Medford-a true piece of Southern Oregon history. ALL furniture, appliances & decor included in sale. Meticulously maintained & brimming with timeless character, house is 2,348 sq ft + basement is 480 sq ft. this treasure sits on a generous 0.28 acre lot with stunning, mature landscaping that creates a private oasis of tranquility. A private garden in the back of the home that leads to a screened in porch. Inside the home Soaring 9-foot ceilings, elegant crown molding, classic wainscoting and gleaming original hardwood floors showcase the craftsmanship throughout the spacious layout. Downstairs a beautiful updated kitchen with marble counters, Bluestar gas range, pantry. Dinning room w/ built in cabinets. Living room has a fireplace and 1 bedroom downstairs & half bath & 4 bedrooms upstairs with a full bath. Updated HVAC & ,new sewer lines. See Video

1320 E Main Street, Medford

$1,249,000
8 Beds 9 Baths 220212846 MLS
Just blocks from downtown, this historic gem blends charm and flexibility. Original fir floors, built-ins, high ceilings, and abundant natural light pair with modern updates. Enjoy the welcoming lawn, pollinator garden, and large covered front porch. The main level offers spacious living and dining areas, kitchen, half bath, and generous entry spaces. A 1-bedroom apartment with interior and private exterior access--includes a kitchen, laundry and full bathroom--a separate additional en-suite bedroom with exterior entry adds versatility. Upstairs are four lovely en-suite bedrooms, one with a balcony, all with updated Renewal by Andersen windows and balcony door. A detached 704 sq ft, 2 bedroom, 1.5 bath, single level cottage with its own address and electric meter provides added flexibility or income potential. With six paved off-street parking spaces, sheds, on-street parking, and alley access, this property offers exceptional possibilities for multi-generational living or investors.

451 N Main Street, Ashland

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

The data relating to real estate for sale on this web site comes in part from the Internet Data Display (IDX) of the Southern Oregon Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information subject to change and should be independently verified. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated: